Bioorganic & Medicinal Chemistry Letters 2006-09-01

Selective COX-2 inhibitors. Part 1: synthesis and biological evaluation of phenylazobenzenesulfonamides.

Wei-Jern Tsai, Young-Ji Shiao, Shwu-Jiuan Lin, Wen-Fei Chiou, Lie-Chwen Lin, Tsang-Hsiung Yang, Che-Ming Teng, Tain-Shung Wu, Li-Ming Yang

Index: Bioorg. Med. Chem. Lett. 16 , 4440-3, (2006)

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Abstract

A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure-activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC(50)'s for COX-1: 23.28 microM; COX-2: 2.04 microM), being active but less COX-2 selective than celecoxib.